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Unsymmetrically substituted dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A convenient scaffold for bioactive molecule design.

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dc.abstract.enA novel approach for the synthesis of unsymmetrically substituted dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones has been developed. This facile three-step method uses variously substituted 1H-benzo[d][1,3]oxazine-2,4-diones (isatoic anhydrides) and 2-aminobenzoic acids as a starting materials. The obtained products were further transformed into N-alkyl-, N-acetyl- and dithio analogues. Developed procedures allowed the synthesis of unsymmetrical dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones and three novel heterocyclic scaffolds: benzo[b]naphtho[2,3-f][1,5]diazocine-6,14(5H,13H)dione, pyrido[3,2-c][1,5]benzodiazocine-5,11(6H,12H)-dione and pyrazino[3,2-c][1,5]benzodiazocine-6,12(5H,11H)dione. For 11 of the compounds crystal structures were obtained. The preliminary cytotoxic effect against two cancer (HeLa, U87) and two normal lines (HEK293, EUFA30) as well as antibacterial activity were determined. The obtained dibenzo[b,f][1,5]diazocine(5H,11H)6,12-dione framework could serve as a privileged structure for the drug design and development.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorTrzybiński, Damian
dc.contributor.authorBieszczad, Bartosz Łukasz
dc.contributor.authorGarbicz, Damian
dc.contributor.authorGrzesiuk, Elżbieta
dc.contributor.authorMielecki, Damian
dc.contributor.authorMieczkowski, Adam
dc.contributor.authorWoźniak, Krzysztof
dc.date.accessioned2024-01-26T11:20:03Z
dc.date.available2024-01-26T11:20:03Z
dc.date.copyright2020-02-18
dc.date.issued2020
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number4
dc.description.versionFINAL_AUTHOR
dc.description.volume25
dc.identifier.doi10.3390/MOLECULES25040906
dc.identifier.issn1420-3049
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/124251
dc.identifier.weblinkhttps://www.mdpi.com/1420-3049/25/4/906
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofMolecules
dc.relation.pages906
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.encrystallographic analysis
dc.subject.encytotoxicity
dc.subject.enheterocycles
dc.subject.enisatoic anhydrides
dc.subject.enunsymmetrical dibenzo[b,f][1,5]diazocines
dc.titleUnsymmetrically substituted dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A convenient scaffold for bioactive molecule design.
dc.typeJournalArticle
dspace.entity.typePublication